text: To 2.76 g (25.0 mmol) of 1-octyne was added 25.0 mL of a 1.07 M solution of diisobutylaluminium hydride (26.8 mmol) in n-hexane while the temperature was maintained at 25–30° by means of a water bath. The solution was stirred at room temperature for 30 minutes and then was heated at 50° for 4 hours. The resultant alkenylalane was cooled to –30°, diluted with 15 mL of dry ether, and treated with 5.35 g (30.1 mmol) of N-bromosuccinimide  while keeping the temperature below –15°. The reaction mixture was gradually warmed to room temperature and stirred for 1 hour before being poured slowly into a mixture of 6 N  hydrochloric acid (50 mL), n-pentane  (10 mL), and ice (10 g). The layers were separated, and the aqueous phase was extracted with pentane. The combined organic extract was washed successively with 1 N  sodium hydroxide, 10% sodium sulfite, and saturated aqueous sodium chloride and then was treated with a few crystals of BHT to inhibit isomerization of the alkenyl bromide. After drying over magnesium sulfate, distillation afforded 3.72 g (78%) of (E)-1-bromo-1-octene, bp 67° (5 mm), n 1.4617. This compound, which contained 4% of 1-bromo-1-octyne, was stored over a few crystals of BHT. H NMR (CDCl): δ 0.92 (m, 3 H), 1.1-1.7 (m, 8 H), 1.90-2.34 (m, 2 H), 5.85-6.30 (m, 2 H).